


Strawberry On Top

by feeling_a_little_hysterekal



Category: Teen Wolf (TV)
Genre: Anal Fingering, Anal Sex, Bottom Jackson Whittemore, Bottom Stiles Stilinski, Doggy Style, Dubiously Consensual Blow Jobs, Endgame Derek Hale/Stiles Stilinski, Everybody wears lingerie, F/M, Feminization if you squint, Feral Behavior, Feral Derek Hale, Girl Penis, Jackson is a Little Shit, Lingerie, Lydia has a dick, M/M, Mirror Sex, Multi, Orgy, Overstimulation, Power Play, Praise Kink, Prostate Massage, Prostate Milking, Rape/Non-con Elements, Rimming, Rough Sex, Stockings, Top Derek, Top Jackson Whittemore, Top Lydia Martin, Watersports
Language: English
Status: Completed
Published: 2019-11-29
Updated: 2019-11-29
Packaged: 2021-02-25 21:28:15
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 5,375
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/21602215
Author URL: https://archiveofourown.org/users/feeling_a_little_hysterekal/pseuds/feeling_a_little_hysterekal
Summary: Jackson spitefully invites Stiles into an orgy with him and Lydia, challenging his sexual capabilities. Stiles, just as spiteful, accepts the challenge.What he doesn't expect is for Lydia to bring her step-brother, Derek Hale into the mix or for Lydia to be versatile.He just might be in over his head.
Relationships: Derek Hale/Lydia Martin/Stiles Stilinski, Derek Hale/Stiles Stilinski, Derek Hale/Stiles Stilinski/Jackson Whittemore, Lydia Martin/Jackson Whittemore, Lydia Martin/Stiles Stilinski, Lydia Martin/Stiles Stilinski/Jackson Whittemore
Comments: 13
Kudos: 446





	Strawberry On Top

**Author's Note:**

> This is very different and yet totally on brand. Yes, Lydia has a dick. This is very experimental. Sterek endgame always.

Jackson examined his apple for any bruises. "I don't think you're man enough Stilinski. You can't handle her." 

Stiles rolled his eyes. "Not that it's actually any of your business, Jackson but I'm not some bumbling virgin. My track record is nice and consistent, thank you very much." 

Jackson snorted and folded his arms looking smug. "Yeah she's got nothing on your little checklist. I guarantee it."

"Is that a challenge, Jackson?" Stiles glared, stepping up close to Jackson. 

"Perhaps. If only to see you run away with your tail tucked, Stilinski."

"Do I get any say in this?" A sharp voice snapped, making both boys jump. 

Stiles turned around to see a very stern Lydia Martin. Arms folded and looking more than a little ticked off. 

"I believe if there's going to be some sort of challenge involving my body I should get a say in it. Don't you agree, Jackson?" Lydia nearly snarled. Painted fingernails digging into her arms. 

"Of course, Lyds!" Stiles interjected. 

"I think Stiles would make an interesting addition to our sex for a day, wouldn't he?" 

Lydia studied Stiles for a moment. 

"Fine. I'm inviting my brother, too. He could use a little change of pace." Lydia said as she turned and walked away. 

"Wait - her brother?" Stiles gawked. 

"Step-brother." Jackson clarified. 

"Is that supposed to make a difference?" Stiles scrunched his nose, somewhat uncomfortable. 

"Getting cold feet already? I told you Lydia is more than you can handle."

"Don't fuck with me. I'm not backing down!"

\------

"Your brother is Derek Hale?!" Stiles gaped at the dude in front of him. He was wearing only black pajama bottoms that did little to nothing to hide the perky dick he bestowed. The guy was huge for a senior. 

Stiles doubted the guy got carded at clubs. Hell he wouldn't have been surprised if he was thought to be one of the bouncers. 

Derek raised an eyebrow at Stiles. 

"Yes, Stiles." Lydia looked bored. "Beacon Hills 'walking wet dream' - as you so eloquently put it the other day, is my brother." 

Stiles gulped. "You heard that?" 

Derek looked almost bored, maybe mildly annoyed, and took a seat on the end of Lydia's bed. 

Jackson smirked. "Deal breaker, Stilinski?"

Stiles clenched his fist. "Stop asking me that. I'm not backing out." 

"Whatever." Lydia waved a hand at Stiles' determination. "It's just sex. We're going to do it with or without you. So you better be sure. I'm not going to waste my time on your inner turmoil." 

Lydia stripped off her clothes save for a pair of white sheer tights. 

Stiles felt his face burn and adrenaline kick in seeing her naked form. Her breasts were small and pink. Perfect to cup his hand around. She had a taught waist and muscled ass, somehow enhanced by the tights. He never realized how fit she was as she carried herself so gracefully. 

He swallowed thickly as she made to sit between Derek and Jackson on the bed, crossing her legs in an almost business fashion, leaving Stiles standing in the middle of the room. 

He felt like he was in a dream as he watched Lydia slip a hand into each of the boy's sweatpants, fondling them. 

Stiles felt his heart racing as he watched Derek grow impressively, dying to see what the hunk looked like. 

He knew what Jackson looked like for the most part. The jerk always had a boner after lacrosse games and wasn't shy about it in the showers. 

Jackson leaned back for a moment, interrupting Lydia's ministrations to push his sweatpants down to his knees. Boner high and proud with a red head. 

Lydia turned her gaze to Derek, who still somehow looked bored, not having said a word the entire time. 

Stiles was painfully hard already in his jeans, fingers twitching with the desire to join in. 

He wanted to see Derek's cock, which was tenting his sweatpants halfway down his right pant leg. 

Derek had to do it for her, and when his cock was freed, it slapped with an impressive thud against his abs. 

'Jesus Christ,' Stiles thought to himself, fisting his shirt in a tight grip, staring at the beast of a cock Derek bestowed. It was veiny with a prominent head peeking from under a tight foreskin. 

Lydia continued stroking, twisting her grip at the tip before pulling down. She turned her attention to Stiles and he suddenly felt very over-dressed.

"Well? Get over here." 

"Wha?"

"Do not make me repeat myself." Lydia scorned. 

"Sorry!" Stiles took two large steps up to her, standing right at her feet. Her face was lined up perfectly with his belt and she sat there for a moment, still casually stroking Derek and Jackson. 

She glanced up, eyebrow raised at Stiles, who was shivering with trepidation and arousal. 

"Do I really have to spell it out for you?"

Stiles flinched, realizing he'd been motionless and quickly undid his belt buckle before freezing again. 

"Wait, are you going to-?"

"I don't know, Stiles." Lydia was starting to sound irritated. "Am I going to blow you or are you going to keep wasting my time?" 

Stiles noticed Derek look at her with something like muted disbelief while Jackson smirked. 

Stiles let out a breath and let his pants and boxers drop to his ankles, shivering in the cool air his cock felt like it was burning, a deep blush working it's way down Stiles' cock. 

Lydia analyzed it for a moment and looked satisfied, leaning forward to press her lips on the tip. 

Stiles flinched, feeling light-headed as every fantasy he'd ever had of Lydia started replaying in his mind all at once in flashes as she teased his length with her plush lips. She made her way back up to the tip and, looking up at him, tentatively licked the underside of his head. 

Stiles' cock jumped at the hint of hot tongue. 

Lydia wrapped her lips around the head and sucked delicately, lapping up beads of mildly salty precum. 

Stiles fisted both hands in his shirt, trying not to grab Lydia's head like he wanted to, enduring her torturous kitten kisses. 

His legs started shaking after a few minutes and he wasn't sure if he was breathing. 

"L-Lydia..." Stiles tried to speak up. 

Suddenly Lydia let go of Jackson and Derek, grabbing Stiles' hips and dropping to her knees, angling Stiles' cock down. She tilted her head back and pushed up, sliding his cock straight down her throat, only stopping when her nose reached his pelvis. 

"L-Lydia!" Stiles yelped, legs nearly giving out and he braced himself on her shoulders as she stayed there. 

"Oh my God, Lydia s-stop you'll hurt yourself!" But he couldn't help the desperate humping of his hips or grabbing the back of her head to hold her there. 

Lydia did not struggle but instead worked herself to swallow. 

Stiles was panting now, lost himself to the heat and constriction of Lydia's throat. Drool and precum frothing along her mouth and dripping slowly down her neck. The only sounds now were his own desperate breaths and Lydia's gagging and sucking.

He flew to edge but he wanted to see Lydia's face. He waited till the last moment, pulling Lydia off his cock to spray cum across her open mouth and face.

It sprayed the roof of her mouth, clung to her eyelashes and cheeks, cascading into her hairline and across her forehead. 

When he finally caught his breath enough to let her go and open his eyes, what he saw was a very disheveled Lydia, covered in cum and looking mildly put out, licking cum around her lips. 

"What a mess." 

"Lydia I'm sorry I-"

"Nice, Stilinski." Jackson snickered from his spot on the bed, leaning back on his arms. "What happened to that 'consistent list' of experience?"

"Shut up." Stiles mumbled.

Derek however was red in the face, cock swollen and visibly throbbing. He was leaning his elbows on his knees like as if he was actually trying to hide it, studying the floor very seriously. 

"Uh..." Stiles didn't know what to say. 

"I'll be back." Lydia pivoted on her kneeling spot to turn away and stand up, walking to her own bathroom to clean the cum out of her hair and face. 

Stiles suddenly felt more vulnerable than ever. Left to stand there with a tacky, wilting cock in the cold. 

"You alright there, Derek?" Jackson poked the brooding man. 

Derek said nothing. 

Jackson eyed his cock and laughed. "Stiles I think you have a fan."

"What?" 

Derek turned a death glare to Jackson, who ignored it and scooted up close, reaching out to grab Derek's burning length. 

Derek clenched his teeth at the touch, grabbing Jackson's arm. 

"I haven't seen him this hard in a long time." Jackson said, stroking experimentally, feeling the heat, bulging veins and erratic heartbeat. 

"Jackson-" Derek growled in warning, concentrating on not cumming. 

That was the first thing Derek had said this entire time and Stiles felt a pleasurable pulse in his cock at the sound. 

"I hope you're ready for more, Stiles." Lydia spoke from the doorway, toweling her partially wet hair. 

"It's been a while since I've experienced the raw energy of a virgin like you. I'm going to have fun." 

"I'm not actually..." Stiles stopped himself correcting Lydia on him being a virgin. Maybe she'd judge him less for losing control so quickly if that's what she believed. 

Stiles swallowed thickly and then eyed Lydia's hips, noticing something atypical. Then he did a double take. 

Lydia was unaware of his stare as she sat on the bed and peeled her tights down and off. A pretty, pink and respectable cock at alert between her thighs. 

Stiles was gobsmacked. How had he remained unaware of this his whole life? 

Lydia noticed his stare now and paused. 

Jackson was finally pushed away by Derek and he also took notice to where Stiles was staring and smirked. 

"Awww is this it, Stiles? Too much for you?" He looked gleeful. 

Lydia scorned at Jackson. "You didn't tell him?" 

Jackson didn't look remotely shameful. "I may have forgotten to mention it."

"Selectively." Derek said, looking extremely ill-humored. 

Lydia didn't let her firey-ness fade. She shook her hair to one side, folded her arms and looked at Stiles. 

"So is this a deal breaker?" 

"No." Stiles said without hesitation. He just had to change his expectations of how this was going to go. 

Jackson looked unconvinced but humored all the same. 

Lydia masked her relief with pride and walked to her dresser, pulling out a box of assorted thigh high socks. "I'm going to ask all of us to wear these. It's my only request." 

Stiles walked up and looked at the choices. White, black, grey, pink, blue, candy cane stripes, white and black polka dots, black spiderwebs and solid red. 

"Umm..." he studied them seriously. "I'll take... the red ones." 

"Nice choice." Lydia said, respectfully. 

"Hand me the black ones." Derek held out his hand, to which Stiles handed them over. 

Jackson peered into the box, looking a little sour. "I guess I'll take the blue ones." 

"And I'll take the white ones." 

Stiles struggled a little pulling them on but when they were finally on he was surprised at how sturdy they felt as well as soft. He felt sexy, which was unexpected and his cock chubbed a bit. 

"They look good on you." Lydia admired, turning him to look at himself in her full length mirror. 

Stiles blushed looking at himself. The fabric seemed to enhance the curves of his thighs. He'd never really thought of himself as sexy or desirable. Sure, not ugly or bad to look at but not... 

"Delectable." Derek had walked up behind them, gazing at Stiles with pure hunger and desire. His pupils blown wide. 

Stiles shivered under his gaze, ears burning. He wasn't sure who he wanted most or what he wanted to do most. He could feel Derek devouring him with his eyes and he wanted it. He wanted to be good for the man. 

Somehow the stockings only accentuated Derek's muscled thighs and it nearly made Stiles drool. 

He was also very aware of Lydia's hot, velvety skin against his own as she pressed into his side. Her boobs caressing his arm as she began to lay soft kisses along his shoulder, moving up his neck. 

A firm hand clutched his right butt cheek, making him jump. Stiles turned to see Jackson. 

"Not bad, Stilinski. Who knew you had such a bubble butt? I don't recognize this from the locker rooms."

"Alright, I get him first. Move." Lydia shoved Jackson aside, hauling Stiles over to her bed and pushing him down. 

"I'm assuming you've never sucked a dick before, either." 

Stiles shook his head. 

"We'll take our time, then." Lydia crawled up to straddle Stiles' face, kneeling on her hands and knees so she faced his dick, as well, long hair draped over her right shoulder and tickling his hip. 

Stiles stared up at the pink, semi-hard penis Lydia endowed. It wasn't very big, about average but Lydia was cleanly shaved save for a meticulously trimmed heart. She wasn't circumcised either. The tip of her pink head peeking out from underneath an almost equally pink layer of foreskin. It was delicate looking and just as feminine as the rest of Lydia. 

He flinched at the touch of her hand as she started to work on him, again. This time starting slow. Just trying to keep him interested. Hot tongue laving at his head. 

He let out a gust of hot breath and Lydia's cock pulsed. 

He swallowed, focusing back to it and tentatively rose up to lick at the shy tip. 

Lydia didn't react like he did but he recieved no criticism so he continued. Tentative kitten licks and sucks to her tip. 

However he did get a shiver when he dipped his tongue passed the foreskin, twirling his tongue around the hidden head and lubing it with saliva. 

Emboldened, he sucked the tip back into his mouth, rubbing his tongue firmly along her slit. 

"Mm!" Lydia flinched and the taste of mildly salty precum burst across Stiles' tongue. Oh now that was delicious and he wanted more. 

He pulled back, Lydia's cock popping out of his mouth obscenely before he pushed back up, licking her frenulum eagerly. 

After another minute or so however, his neck was severely sore and his jaw was cramping. He pulled Lydia off of his dick by her shoulders, tossing her up, over and behind him, sitting up to crawl over to her. 

"I had plans, y'know." Lydia said, irritation colored with humor as she spread her legs open for him. 

Stiles ignored her as he lay on his stomach, much happier now that he didn't have to strain to reach her. He took her head back into his mouth and worked about half the length into his mouth, trying hard to relax his gag reflex. 

"But I'm sure Derek wouldn't mind taking over for me." Lydia continued. 

"Mmh?" Stiles felt the bed dip as Derek immediately placed himself behind Stiles, grabbing his hips and pulling him up onto his knees, Lydia's dick still in his mouth. 

Derek's large hands encompassed his ass, using his thumbs to firmly pull his ass cheeks apart, baring his hole to the air. 

"Ah! Geez..." Stiles looked back at Derek whose eyes were blazing with arousal. 

Stiles was no stranger to his prostate - however he definitely had never had himself spread open like this, a tremor building up in his spine at the strength behind Derek's grip. 

Derek growled at the sight of Stiles' hole twitching under his gaze. He wasted no more time and spat hot and harsh onto the hole, making the boy jump again. 

Derek dived down to devour the sensitive skin, licking, sucking and prodding. It made Stiles moan around Lydia who in turn bit her lip at the vibration. 

"Well I'm not going to be left out of this." Jackson grumbled, climbing onto the bed. 

He straddled Lydia's hips, suggesting she take him into her mouth, too. 

"Oh, honey please sit down next to me. I don't want to miss out on this." Lydia patted Jackson's hip, who cursed and all but flopped next to her. 

It was true, the sight of Stiles in front of her on his knees, back arched into the air as Derek all but ate him was something she wanted burned into her memory. 

In fact..., "Babe, grab my phone." Lydia whispered, tapping Jackson's thigh in a hurried manner. 

Jackson sighed and grabbed it off her night stand, handing it to her. 

Lydia quickly opened the camera and began filming. 

Jackson busied himself with taking one of her nipples into his mouth as Lydia jerked him slowly. 

Stiles felt like he was melting under the heat of Derek's tongue. He could feel his hole softening and giving to the muscle, tightening up again as soon as it left him for even a moment. 

Derek licked his lips as if Stiles was the most delicious thing he'd ever tasted, kneading Stiles' cheeks aggressively with his fingers. 

"Ow, Derek!" But Stiles couldn't help the moan or deny the burn of pain adding to his pleasure. He gasped, open-mouthed around Lydia's length when Derek viciously worked his thick, burning tongue _inside_ him. 

"Sh-shit!" Stiles clenched his fists, momentarily forgetting Lydia altogether as he pressed his face into the mattress. 

"H-Hey," Lydia's quivering voice brought him back as she worked her fingers through his unkempt hair. She was clearly more turned on than she had been in a while. 

"Tell me what you feel." 

Stiles let out a shaky sigh, staring into her eyes with blown pupils. 

"H-He's got his tongue in-nside of me."

"Yeah, how is it?" Lydia swiped his sweaty bangs off his forehead. 

"Hot. So f-fucking hot." 

Lydia took herself in hand, stroking upward to twist her wrist at the tip. "What else, Stiles? What else is my brother doing to you?" 

"U-umm," Stiles stuttered, closing his eyes. "W-well his hands... they're so big and strong. I want them in- hah!"

Stiles gasped as Derek dipped two thick fingers inside, slipping all the way to the knuckles and working his tongue deeper between the scissoring digits.

Lydia's cock was strained, now a burning red and thicker with arousal. Slick sounds were loud in Stiles' ears as she leaked profusely in her own hand. Her foreskin pulled down and back up with every stroke. 

When Derek found Stiles' prostate he keened, toes flexing and legs shaking. 

"F-fuck I'm gonna cum!" Stiles' second orgasm of the night was boiling right at the edge, hot and coiled.

Suddenly Lydia was slipping out from underneath him, jostling him as she nearly leapt over, pushing Derek aside with considerable strength. 

Before Stiles could even register what she was doing, she mounted his hips and slammed home. 

Stiles' eyes and mouth flew open in shock at the intrusion. He'd had plenty of dildos that surpassed Lydia's size but for some reason bare skin just made it so different. That and all he really had for lube was Derek's drool and whatever precum Lydia had collected. 

His insides burned as she immediately set in a harsh, pounding pace. Gripping the sheets in a death grip Stiles did his best to ride it out. 

The slide of her stocking clad thighs along his ass was divine and the slap of her tiny ballsac along his scrotum was teasing. 

"Ohh, Stiles, you're so hot inside." Lydia crooned, leaning forward to put almost all of her weight on his back. She was small enough he could do hold her up without too much trouble. His skin prickled as her nipples and hair tickled his back. 

Stiles finally felt himself beginning to relax, resting his head back on the sheets as Lydia humped him. A moment later he had Jackson sitting with his lap at Stiles' face. 

When he looked up Jackson was looking less than humored with an angry erection. 

"Open your mouth."

Stiles sat up a little in order to take Jackson. Jackson was a good seven and a half inches and twice the width of Lydia complete with a bulbous head. 

As soon as Stiles opened his mouth Jackson hunched his hips up and pushed Stiles' head down by his neck. 

Stiles gagged viciously and stiffened before struggling, pushing against Jackson's stomach to get away. 

"Uh-uh, you want cock so bad you're gonna learn to suck it properly." He pulled Stiles up, who gasped obscenely, a thick string of saliva connecting him and Jackson's dick. 

"Y-you, fuckker." His voice was immediately hoarse and he fell into a coughing fit. 

"Jackson be nice!" Lydia scorned from above. 

Derek was pissed however and stepped up onto the bed which creaked under his weight. 

Derek pulled Jackson to his cock in a harsh twist, hooking a thumb into his mouth to force it open and stuffed his cock as far as it would go down Jackson's throat. 

"Why don't you show him then, huh, Jackson?" Derek growled. 

Jackson gagged just as Stiles had, his face instantly burning red, a vein bulging at his temple as Derek held onto his head, fucking into his throat. 

Stiles had to duck as Jackson's legs started kicking. Only then did Derek let him up. 

"Boys!" Lydia shouted, having stopped her fucking of Stiles since Jackson started his assault. 

Derek slapped Jackson as he gasped for air - not hard but definitely not lightly - before shoving him away. 

Jackson got the message and laid back down against the pillows, coughing wetly and wiping his face. His boner having gone down significantly. 

Stiles decided to ignore him for a while. He was hurting from Jackson's barrage on his throat. Let the guy feel bad for a minute. 

Derek walked behind Lydia, standing at the end of the bed. Somehow he'd procured a bottle of lube and was coating his fingers generously. 

Lydia continued a smooth rolling of her hips, the tip of her cock brushing ever so lightly across Stiles' prostate, who sighed pleasantly. 

When Derek slipped his middle finger inside of Lydia, Stiles felt her flex inside of him and he moaned a little at the sensation. 

Soon Lydia was less fucking Stiles and more pressing deeply into him as Derek fucked her with four fingers. The jostling of his hand inside of her was reverberating into Stiles as well as the pulsing of her leaking dick. 

The sound of Lydia moaning at Derek's ministrations made him clench around her in arousal as well as jealousy. 

He'd had those fingers in him mere minutes before and he wanted them again. 

"Ohh, fuck, Derek!" Lydia moaned as her prostate was pressed and massaged. 

"Nhhh." Stiles moaned in response feeling the pulsing of Lydia and imagining what she must be feeling, asshole quivering around her. 

The bed dipped again as Derek lined himself up and pushed ever so slowly into the strawberry blonde. 

Lydia fell forward once again onto Stiles, gasping into his ear, legs quaking as she took Derek's girth. 

Stiles almost felt like he was taking it, too. Lydia swelling inside him, the pressure on his prostate increasing. 

Derek let out a sigh as he bottomed out in Lydia. He was not prepared for the dual gasps and moans as he began fucking, however. Stiles making bitten off whimpers and panting right after Lydia's moaning and mewling. 

It was dangerous when he looked down, he could see Lydia resting her cheek on Stiles' shoulder, facing the left and gazing up at him while Stiles mirrored her, gazing up at him from the right. 

Shit if that didn't get his ego going. 

"You fucking like that?" Derek picked up the pace, slamming into Lydia, who keened while Stiles whimpered. 

"Fuck yes fuck me, Derek." Lydia gasped. 

Stiles nodded, panting and sweating at holding Lydia up. 

_'Fuck me fuck_ me _!'_ Stiles thought desperately, trying to imagine the rough pounding he was currently bracing Lydia into was for him. 

"Fucking couple of sluts." Derek growled, actually grabbing onto Stiles' hips to fuck even harsher into Lydia. 

The grip made Stiles moan even more and he collapsed forward, ass up face down, thus putting Lydia in the same position. 

Lydia seized up, hips lighting up again, humping into Stiles as she cried, cumming deep inside of Stiles. 

The tip of her cock jabbed into Stiles' prostate repeatedly and while he did not cum, he thought he would, freezing up on the assault of stimulation, moaning whorishly with Lydia's cries. 

Derek had never experienced something so hot. Two people stroking his ego as he fucked them. He was so close to cumming and continued to fuck. 

He climbed up onto the bed, squatting over the pair and fucking like an animal. 

Lydia was not recovered and the pace was quickly too much for her. 

"Derek, ow! You're being too rough!" Lydia shouted. 

He was fucking into her aggressively and looked almost feral, snarling with effort. 

He felt sympathy for Lydia but also an uncomfortable pang of arousal as Derek's massive balls starting to slap against Stiles' from how hard he was pressing the two together. 

Derek hooked a hand into her mouth.

"Yerek! Shtoh!" Lydia pleaded, head bent back. 

Stiles couldn't hold her up any more, his spine giving out and thus harshly pulling Derek out of Lydia with an audible shlup!

"Son of bitch." Lydia groaned, rolling off and away, cupping her abused hole. 

Derek growled in frustration and stood up, pacing and shaking his dick to stave off his orgasm. 

Stiles watched him for a few laps while Jackson comforted Lydia. He caught sight of the bottle of lube Derek had used, snatching it up and shamelessly stuffing the tip inside himself. He squeezed a copious amount of the cold substance in before tossing it aside and calling out to Derek, voice dry. 

"Derek." 

Derek stopped at looked at him, still looking like an animal. 

Shivering with need, he arched his ass up, reaching back behind him to spread his already slightly gaping hole, the cold making it wink and squelch, lube dripping down his balls. An offering on display. 

Derek strode up to him without delay, hauling him to the edge of the bed by the hips and slamming home. 

Stiles cried out in shock of the heat and sheer size of Derek. Lydia was absolutely no match. Nor Jackson. He was grateful for the lube and he was determined to take Derek's cock when Lydia couldn't. 

Derek began pounding him with the same force as he had Lydia and Stiles quickly lost himself to pain and pleasure. It was a strange pain, though. There were parts inside him that had never been reached before and were sore with inexperience. 

"Ohh, fuck, Derek!" 

Derek was encouraged and widened his stance more to get impossibly deeper. 

"Oh shit! Oh, fuck! Derek I'm gonna cum!" Stiles clung to the sheets as he flew, legs shaking with orgasmic tremors. 

Derek didn't change his pace and Stiles was crying out in ecstasy. His cock impregnating the sheets. Probably soaking straight into the mattresses interior. 

Derek fucked him through the contractions and when they were over he hauled Stiles to a standing position then off his feet, an arm hooked under each leg. 

Stiles felt tiny being manhandled and forced to trust Derek when he was vulnerable... and he didn't want anything else. 

Derek turned around to face the mirror and entered him again, this time fucking straight up into his prostrate. Stiles moaned at the sensation and watched his reflection bounce pitifully. He was totally in Derek's control and at his mercy. 

"Ohh, God! D-Derek!" A third orgasm ripped through him with hardly any warning. Cum launched and splattered haphazardly on the mirror and floor. 

"Fuck, Stiles." Derek growled into the boy's shoulder, suddenly pulling him up and off Derek's cock, flipping him around to face each other, never letting his feet touch the ground.

Derek lowered him back down, hands firmly gripping Stiles' ass until he felt his cock head touch. He faked dropping Stiles, grabbing him by the thighs at the last moment. 

Stiles yelped at the drop, fingernails digging into his shoulders with a death grip, and moaned whorishly as he was speared by Derek's cock again. 

"Ohhhh," Stiles' voice took on a slightly high pitched tone as the pressure and angle of Derek's dick was reversed. Derek's flared head passing over his prostate with intense pressure. 

Derek returned to bouncing Stiles up and down on his cock, panting with the effort as they gazed at each other. 

Stiles felt like his insides were melting and molding around him, permanently remembering his shape. 

"Fuc-cking-g h-hell, Der-rek I'm-m c-cum-ming 'gain!"

Derek groaned animalisticly. "Yes, yes, fuck yes. Keep cumming on my dick. Good boy."

Stiles felt his ass bear down, trying to swallow the piece whole. He couldn't resist his face contorting like he was in pain, pressing his face into Derek's neck and wrapping his arms around him to hang on for dear life, milking Derek for all he was worth. 

Derek groaned, squeezing Stiles back down onto his dick to appreciate the contractions. The feeling of Stiles' cum painting his abs adding to his lust. 

Stiles was breathless as Derek walked them to the bed, grinding and rolling his hips up into Stiles. He had been so horny for so long and was so desperate to fuck that it almost felt like his dick forgot how to cum. 

"Derek, s-slow down." Stiles whimpered as Derek went back to fucking. Their sweaty skin slapping loudly against each other. 

"I will fuck you and you will like it." Derek snapped, gripping Stiles' hair with his fist, bending his head back to expose the beautiful, pale neck. 

"I don't think I can cum anymore, ah!" Stiles winced as he was over stimulated, his prostate fatigued. 

"I doubt that." Derek turned Stiles around, facing the mirror yet again. 

Stiles watched as Derek took Stiles' wilting cock in hand and stroked along the head. 

Stiles nearly bit his tongue with how he snapped his teeth shut, throwing his head back at the barrage of sensation on his post orgasm sensitive head. 

"D-Derek it's too much!" 

Derek seemed to be really into this torture thing, groaning and looking close to cumming as he watched Stiles squirm desperately. 

"You're so fucking hot, Stiles. You learned today that women can have prostates. Well did you know men can squirt, too?"

Stiles was trembling and drooling, tears burning his eyes as he bounced on Derek's lap, cock hard again. 

He shook his head, unable to speak. 

"Well I want you to squirt for me, baby. You've done so good today." 

The praise was really getting to Stiles and despite being totally overwhelmed, he felt another orgasm flying to the surface. He threw his head back on Derek's shoulder, crying out as Derek clenched his teeth, thrusting up one last time to cum deep inside, snaking a hand to press against Stiles' bladder right as his orgasm hit. 

A strong, audible spray of clear urine burst from his cock with a mean hiss. 

Stiles was actively crying as he listened and watched his piss spray all over the wooden floor. 

Derek seemed to really get off on the sound as his legs were shaking with orgasm, rolling up into Stiles to press his cum as deep as possible. Their stockings getting soaked by the splashing on the floor and dripping down Stiles' thighs. 

When the stream began to taper Stiles' cock bounced with orgasmic contractions and when it was finally over he slumped backwards across Derek, who was splayed out looking just as exhausted. 

Stiles hiccuped from his tears. Embarrassment evident but the cloud of post orgasm overtaking him quickly. 

He and Derek fell asleep completely unaware of Jackson bouncing desperately on Lydia's lap, both completely taken by what they witnessed, crying out as they came together and falling into the same sleepy bliss. 

"You fuck'rs bett'r clean 'at piss up." Lydia mumbled before passing out.


End file.
